The Highest Level of Generosity Has Nothing To Do With Money | Ryan Leak

4 May 2026 · 7 min · 3 chapters

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In short

Ryan Leak discusses generosity beyond money, using Jewish “levels of generosity,” anonymous giving, and the idea that the highest generosity is empowering others to earn for themselves (“teach them how to fish”). He also addresses how to respond to people who repeatedly ask without acting (“ask holes”) and how to shift from enabling to empowerment.

Guest background

Ryan Leak is a speaker and leader connected to causes that raise money for single moms. He shares personal history of receiving grace and support after his father’s stroke, including a teacher (Mrs. Holstead) paying his tuition.

Key claims

Giving can be ego-driven; anonymous giving reduces ego. The highest level is positioning someone to make money themselves. Refusing repeated requests can be “peace or pause.” Time and wisdom may be more valuable than money.

Notable examples

Rabbis with coins on their robes so the poor could take without knowing; coins placed in mailboxes so receivers knew but not the giver; Mrs. Holstead paying tuition after financial hardship.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Levels of Generosity

0:31 to 3:16

Exploration of different levels of generosity and their impacts.

“How do you know when to give or who to give to?”

Empowerment vs. Enabling

3:16 to 4:25

Discussion on the balance between helping others and empowering them.

“for people aren't willing to learn how to fish for themselves.”

Personal Stories of Kindness

4:25 to 5:24

Sharing personal anecdotes to illustrate the power of generosity and support.

“I got some ask holes in my life, for sure.”
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Transcript

Automatic transcript. May contain errors.

0:00Hey, Mama.

0:01Ryan Leak:Thanks for making all my favorite recipes. Hi, Ma. Thanks for your unfiltered advice. Hi, Mom. Thanks for always being by the phone. Hey, Mom. Happy Mother's Day. When you ship UPS Air at the UPS Store, your items arrive on time or your money back. Guaranteed at no extra cost. Exclusively at the UPS Store U.S. retail locations. Visit the upsstore.com slash air shipping for full details. Terms and conditions apply. Send your Mother's Day gifts at the UPS Store and we'll get your gratitude there on time. Hi, my name is Lewis Howes and welcome to the Daily Motivation Show.

0:42How do you know when to give or who to give to? Yeah. So for us, we have several and being a speaker is kind of nice because you get to meet so many different kinds of people doing all sorts of different things. and you know if it's a cause you know there's somebody on our team she helps raise money for single moms and I was like that's so awesome and she had just joined our team and so I just I looked at my wife I said I said hey what do you what do you think about this organ say hey could you send me the website we send the website and we just we just give scripture talks about not letting the left hand know what the right hand's doing when it comes to generosity like the the more you're involved in it, the, the, the more your ego can get involved.

1:30In fact, in Jewish culture, we're getting deep into generosity. There was eight levels of generosity. Really? Yeah. Eight levels. The first level was where you, um, you give, but you give with a grudge. Begrudgingly. Yeah. I mean, yeah, you can have it. Yeah. Frustrated. Yeah. But it goes all the way to, um, each level has a different level of ego attached to it. Sometimes you can give with a smile on your face, but you don't give enough. You need 100, I go, hey, here's Siphi. But I smile, I got you. But then there were actually like rabbis that would walk around towns and they would keep coins on the back of their robes.

2:09So people, the poor could actually grab money off of their robes, but they didn't actually know who it was. They kept moving. Wow, interesting. And then there were other times, different levels of generosity, where they would actually put coins in poor people's mailboxes back then, if you will. So they knew who the receiver was, but the receiver didn't know. Very interesting. So you don't know that it's me. Then there's anonymous giving. So we like to do anonymous giving where our friends get supported. They're like, man, you won't believe what happened. I'm like, I do believe what happened. But it's like the more you're involved, the more ego that is there, the highest level of generosity is actually not giving them money.

2:49it's putting them in a position to make money themselves. That's the highest level of generosity. It is not giving them fish, it's teaching them how to fish. Sometimes people don't want to learn how to fish. No. They say they want to, but really the work and time and energy that it takes to invest in generating fish, generating money, they want the easy relief now. Yes. That's the hard thing, though. It's like, how do you know if someone in your life for people aren't willing to learn how to fish for themselves. And they're always coming back for more. How do you navigate that from being an enabler to someone who's empowering?

3:29Totally. You know, for me, I'm always, I mean, again, it goes back to peace or pause. There's people that we've given to on one month, and then the next month they ask, but just say, hey, no, not this time. And that's just peace or pause for us. sometimes I'll tell a friend you don't need my money you need my mind if I gave you an hour of my time the money you're asking for you're asking the wrong question to the wrong person if you have somebody like my phone number in attention you should be asking me for 30 minutes does that make sense that goes back to them even if they took it they may not act on it you know what I mean they may not act on the wisdom So they have to be ready for that.

4:14You know, they have to want it and seek it out. That's what my friend calls an ask hole. An ask hole is somebody that asks the same questions over and over again. Doesn't. But doesn't do anything about it. Yeah. I got some ask holes in my life, for sure. But, man, I just, I think where my posture towards humanity and other people, the chill nature of that, I think, comes from the fact that, And so many people in my life gave me a shot when they shouldn't have. They gave me a pass. And so it's hard for me to hold people to the letter of the law. It's not that I don't get mad or I don't get bothered.

4:57It's just that I know that there was somebody that should have been mad at me and wasn't. And talked to me in a tone that was respectful. and showed me a lot of grace. So it's hard for me to hold people to the letter of the law when I've been given so much that I could go on forever telling you stories about, like when my dad had a stroke, I was at that private school. We were getting ready to leave that private school because we couldn't afford to be there anymore. And there was a freshman English teacher named Mrs. Holstead who came to my mom and she says, hey, me and my husband see your boy's potential.

5:34We'll pay for their tuition. Wow.

5:43I have a brand new book called Make Money Easy. And if you're looking to create more financial freedom in your life, you want abundance in your life, and you want to stop making money hard in your life, but you want to make it easier, you want to make it flow, you want to feel abundant, then make sure to go to makemoneyeasybook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money this moment moving forward. We have some big guests and content coming up. Make sure you're following and stay tuned to this episode of The Daily Motivation Show.

6:24Thank you so much for listening to today's episode of The Daily Motivation, and I hope you have an amazing rest of your day. If you enjoyed this episode, make sure to click the link in the description. that will take you to the full episode of our main podcast on the School of Greatness. And if you are loving the daily motivation, please follow us over on Apple Podcasts and Spotify and leave us a review over on Apple Podcasts right now. And if you want more exclusive content and ad-free listening experience, make sure to subscribe to our Greatness Plus channel on Apple Podcasts right now. And if you want to get even more inspiration from our world-class guests and learn how to improve your life and take it to the next level, then make sure to sign up for the Greatness newsletter and get it delivered right to your inbox over at greatness.com slash newsletter.

7:14Again, have an amazing day and I'll see you tomorrow with another episode of the Daily Motivation Show.

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Check out the full episode: https://greatness.lnk.to/1920DM

Ryan Leak didn't grow up with resources. When his dad had a stroke, his family was about to be pulled out of private school because they couldn't afford it. Then a freshman English teacher showed up and paid their tuition. No fanfare. Just belief.

That moment shaped everything.

Now Ryan breaks down the eight levels of generosity from Jewish tradition and where most people get stuck. Giving with a grudge. Giving with a smile but not enough. Giving publicly when it should be quiet.

The highest level? It's not the check. It's the connection, the time, the mentorship that changes what someone is capable of earning themselves.

And when people keep coming back without doing the work? Ryan's answer is direct: "You don't need my money. You need my mind."

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